2-Chlorobutane → p-(2-Methylbutyl)toluene

HRID 1579822Notes

Reaction equation

HRID 1579822 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[CH:10](Cl)([CH2:12][CH3:13])[CH3:11].[K]>C1(C)C=CC=CC=1>[CH3:11][CH:10]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 65632-ChlorobutaneHCID 77224-Methylbenzyl chlorideHCID 5462222Potassium

Product 1

HCID 10877446p-(2-Methylbutyl)toluene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
50 °C

Procedure

0.05 Mol of p-methyl benzyl chloride and 0.05 mol of sec.-butyl chloride were dissolved in 100 ml. of toluene. The solution obtained was added dropwise to a toluene solution containing 0.1 mol of potassium metal with thorough stirring while obtaining the temperature of the solution at 20° to 30°C. After the addition, the temperature of the solution was raised to 50°C. with thorough stirring to complete the reaction. After the reaction, the product became black violet, and a white powder was precipitated. The resultant product containing the unreacted matter and by-products was distilled to afford 3-methyl-4-(p-tolyl) butane. The resulting product was used in the following Examples.

Workup

  1. customThe solution obtained
  2. customwhile obtaining the temperature of the solution at 20° to 30°C
  3. additionAfter the addition
  4. stirringwith thorough stirring
  5. customthe reaction
  6. customAfter the reaction
  7. customa white powder was precipitated
  8. additionThe resultant product containing the unreacted matter and by-products
  9. distillationwas distilled

Sources & evidence

ORD record
ord-f81e55f7f82746a98c201e51ff527a39
Source dataset
uspto-grants-1976_01
Patent number
US03931348

Reaction notes

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